Ortho-nitrobenzoic acid, 5-nitrofurfurylidene hydrazide



United States Patent 1 Claim. (Cl. 260240) ABSTRACT OF THE DKSCLOSURE The new chemical compound o-nitrobenzoic acid, 5- nitrofurfurylidene hydrazide of the formula having valuable properties in the control and treatment of poultry coccidiosis.

Cross reference related This application is a division of copending application S.N. 514,678, filed Dec. 17, 1965, now US. Patent 3,330,724, issued July 11, 1967.

This invention relates to a new heterocyclic compound of the furan series, and more particularly to a S-nitrofuraldehyde in which the carbonyl oxygen is replaced by an ortbo-nitrobenzoylhydrazone. The new compound which has been the empirical formula C H N O and a molecular weight of 304,228 has the following structure The new compound is a solid, odorless substance of yellow color and has a melting point of ZOO-202 C.

It is soluble in alkaline media and in view of its slightly acidic nature forms water-soluble salts analogous to a number of sulfa drugs wherein the hydrogen of the nitrogen atom adjacent to the carbonyl group may be replaced by a number of alkaline metals and ammonium.

On analysis the new compound was found to contain:

Carbon, 47.38% (calculated value 46.88%) Hydrogen, 2.65% (calculated value 2.60%) Nitrogen, 18.41% (calculated value 18.26%)

The compound may be prepared by interaction of o-nitrobenzhydrazide and a S-nitrofurfurylidene derivat-ive whose carbonyl group is reactive with the hydrazine moiety thereof. Such derivatives of S-nitrofuran are, for example, S-nitrofurfural, its .acetals or lower acylals.

Among the lower acylals of S-nitrofurfural its diacetate is especially suitable for the synthesis of the new com pound. Its formation from 5-nitrofurfurylidene diacetate and o-nitrobenzhydrazide proceeds in accordance with the following equation:

ll 0 H CNHNH: zN CH=(OCCH) t l a The following example will serve as an illustration of the preparation of the new compound:

Example 1.-o-Nitrobenzoic acid, S-nitroturfurylidene hydrazide 25 grams (0.13 mole) of o-nitrobenzhydrazide were refluxed for two hours with 33.5 grams (0.138 mole) of S-nitrofurfurylidenediacetate in the presence of 500 ml. of denatured ethanol, 11 ml. of water and 11 ml. of sulfuric acid. The mixture was cooled and filtered and the resulting condensate was washed free of acid with denatured ethanol in water. The material was dried at C. and the final product was obtained in a yield of 39 grams (92.9%). Its melting point was determined at ZOO-202 C.

As described in the copending application S.N. 514,678, filed Dec. 17, 1965, now US. Patent 3,330,724, issued July 11, 1967, the new compound and its water soluble salts have unique and valuable therapeutic properties in the control and treatment of poultry coccidiosis.

What we claim is:

1. Ortho-nitrobenzoic acid, 5-nitrofurfurylidene hydrazide represented by the formula:

and its water-soluble alkaline metal and ammonium salts.

References Cited UNITED STATES PATENTS 3,290,213 12/1966 Carron 26'0240 XR FOREIGN PATENTS 649,734 7/1964 Belgium.

OTHER REFERENCES Stradins et al.: Latviajas PSR Zinatnu Akad. Vestis, 1958, No. 1, pp. 113 to 120.

Zajdela et al.: Unio Intern. Contra Cancrurn, Acta vol. 20 1-2), pp. 233 to 239 (1964).

JOHN D. RANDOLPH, Primary Examiner. 

